methyl 2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-α-D-xylo-hexopyranoside | 269065-37-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-α-D-xylo-hexopyranoside
• CAS: 269065-37-4
• 化学式: C₂₃H₂₅NO₇
• 分子量: 427.454
• InChiKey: GWHRMPIBUSINNB-GJPOJAMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  100.16
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-α-D-xylo-hexopyranoside 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以93.9%的产率得到methyl 2-acetamido-2,4-dideoxy-α-D-xylo-hexopyranoside
  参考文献：
  名称：

  Synthesis of 4-deoxy analogues of 2-acetamido-2-deoxy-d-glucose and 2-acetamido-2-deoxy-d-xylose and their effects on glycoconjugate biosynthesis

  摘要：

  4-Deoxy analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-xylose were synthesized and evaluated as inhibitors of glycoconjugate biosynthesis. Methyl 2-acetamido-2,4-dideoxy-beta-D-xylo-hexopyranoside (11) showed a reduction in [H-3]GlcN and [C-14]Leu incorporation into hepatocyte cellular glycoconjugates by 89 and 88%, of the control cells, respectively, at 20 mM, whereas the free sugars, 2-acetamido-2,4-dideoxy-alpha,beta-D-xylo-hexopyranoses (15), showed a reduction of [H-3]GlcN and [C-14]Leu incorporation by 75 and 64%, respectively, at 20 mM. The acetylated analogues of 11 and 15, namely methyl 2-acetamido-3,6-di-O-acetyl-2,4-dideoxy-beta-D-xylo-hexopyranoside and 2-acetamido-1.3,6-tri-O-acetyl-2,4-dideoxy-alpha,beta-D-xylo-hexopyranoses, showed a greater inhibition of [H-3]GlcN and [C-14]Leu incorporation at 1 mM compared with their non-acetylated counterparts, but were toxic to hepatocytes at concentrations of 10 and 20 mM. Corresponding derivatives of 2-acetamido-2,4-dideoxy-L-threo-pentopyranose showed no biological effect up to 20 mM, suggesting that the C-6 substituent is important for the biological activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00314-6
• 作为产物：
  描述：

  D-GlcNAc 在 吡啶 、 磺酰氯 、 三正丁基氢锡 、 乙酰氯 、 1,1'-偶氮(氰基环己烷) 作用下， 以 甲苯 为溶剂， 反应 26.0h， 生成 methyl 2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-α-D-xylo-hexopyranoside
  参考文献：
  名称：

  Inhibition of microbial β-N-acetylhexosaminidases by 4-deoxy- and galacto-analogues of NAG-thiazoline

  摘要：

  NAG-thiazoline is a well-established competitive inhibitor of two physiologically relevant glycosidase families-beta-N-acetylhexosaminidases (GH20) and beta-N-acetylglucosaminidases (GH84). Based on the different substrate flexibilities of these enzyme groups, we designed and synthesized the 4-deoxy derivative of NAG-thiazoline aiming at the selective inhibition of GH20 beta-N-acetylhexosaminidases. One GH84 and two GH20 microbial glycosidases were employed as model enzymes for the inhibition assays. Surprisingly, the new compound 4-deoxy-thiazoline exhibited no activity inhibition with either of the enzyme families of interest. Unlike with the substrates, the 4-hydroxyl group of the inhibitor's sugar ring seems to be crucial for binding the inhibitor to the active sites of these enzymes. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.066